🤖😬 AI is coming for your job (application)

🎃 Now THAT’S what we call a “Great Pumpkin,” Charlie Brown. Not only did Connecticut native Alex Noel win this year’s Topsfield Fair giant pumpkin contest with a record-breaking 2,507 pound pumpkin, but he did it just one day after the arrival of his first child. Awwww.

🤤🍎 BTW: Remember those stunning fall Matria dinners this week? Today’s the day to enter to win a free pair of tickets (a $278 value!). Become a member and enter the giveaway here (you get an entry for each night).

👀 What’s on tap today:

Up first…

Are you job hunting? Hiring? There’s an AI bot for that. As the labor market cools, employers and employees have entered an AI “arms race” to hack the hunting and hiring processes, according to the Globe. And, spoiler: Both sides have complaints.

Here’s what to know:

🤖 AI is the new hiring manager. Fun fact: More than four out of five employers are already using AI in their hiring process, including pretty much every large company, according to the U.S. Equal Employment Opportunity Commission. Bots are writing job postings, parsing through resumes, and even conducting eerie screening interviews.

🙋 It’s also the new career coach. On the other side of the screen, job seekers are using AI tools to write resumes and cover letters, customize them for specific postings, and practice mock interviews. One survey found that 39% of candidates said they used AI during the application process. Of that sample, ~50% used it to write their cover letters and resumes. 

🚀 Which means we’re starting to lose the “human” in human resources. What happens when AI helps more and more candidates get their applications past AI screeners? There are too many applications for a person to review, and companies turn to AI interviews to help them whittle down the field. “So it’s just becoming a circular problem,” Alexa Marciano, managing director at a recruiting firm, told the Globe.

🥲 To be fair, AI has helped plenty of folks on the job search. Alyssa Hammond, Bentley University’s director of undergraduate career development, thinks AI can be genuinely helpful for young job hunters. It can scour thousands of job postings to find the ones worth applying for, or help with a first draft of a resume or cover letter, she said.

🚩 But not without some major red flags … To name a few: Concerns about automated bias (this study found bots were heavily biased against Black and women-associated names); or AI bots exaggerating — if not flat-out making up — applicants’ qualifications (which is becoming harder to flag, even for humans). Not to mention, being interviewed by an AI bot can also be … off-putting.

🧑‍💻 Red flags or not, don’t expect AI use to slow down. As the AI “arms race” continues, experts say we can expect more AI interviews, and more applicants having to use it just to keep up. Bullhorn chief executive Art Papas thinks even applicants will have their own AI bots soon: “‘Talk to my AI bot. It can answer most questions for me,’” he said.

💬 Interested? You can read the full story here.

💬 P.S. If you’re under 30 and smoke cigarettes (or used to!), we’d love to talk to you for an upcoming story! Email Gia at [email protected].

🖼️🍂 You don’t need PYO pumpkins to make October magical — you just need a museum day. MFA Boston is bringing the vibes this season with free admission on Indigenous Peoples’ Day (Oct. 13) and UNIQLO Free Admission Day (Oct. 25), plus $5 nights that glow extra bright with Diwali’s lights + dance (Oct. 19) and the newly-launched $5 Third Thursdays series (Oct. 16). Plan your visit now and make this fall a little more cultured (and a lot more fun).

🏘️ We’re adding “BIG new housing policy” to our 2026 bingo cards. In a new survey, 43% of Bostonians rated the city’s efforts to tackle its housing crisis “poor,” and many indicated they’d be more willing to support aggressive policy changes. Despite Mayor Wu’s beefy investments in affordable housing, production declined during her first term (though it didn’t cost her in the polls). So some experts say now might be the *perfect* moment for Wu to take a big swing on potentially controversial policies to put a real dent in the problem.

🏒 TD Garden’s gotta make some room in the rafters. ‘Cause on Jan. 15, the Bruins will officially retire No. 33 in honor of Zdeno Chara (a.k.a. Big Z). The gigundo 6’9” defenseman played for the B’s from July 2006 to 2022, serving as team captain the entire time, and leading the B’s to three Stanley Cup Finals, including a win in 2011. The night will mark the franchise’s 13th retired number in 100 years. Warning: This video of him finding out might make you happy cry.

🌲 This is your chance to hear “Northern Attitude” live. Noah Kahan is coming back to Boston for one night only! He’ll be putting on an intimate show at MGM Music Hall on Nov. 20 to support The Busyhead Project and the Red Sox Foundation. Want tickets? Slow your roll. To get them, you’ll need to “request” tickets by price point (they start at $107) before 11:59 p.m. on Oct. 12. On Oct. 15, you’ll find out if you got them. In the meantime, we’ll be playing the Fenway live album on repeat.

🥪 BREAKING: You can eat lunch in Boston for less than $10. No, this isn’t fake news. Just ask Dylan Bloomfield, who’s been sharing his journey to find lunch Downtown for $7 or less. Inspired by his efforts, WBUR asked its readers (and Bloomfield himself) for their best cheap lunch recs in the city, and they absolutely came through. See: Two hefty pizza slices for $7 at Mortadella Head and $8 pork banh mi at Banh Mi Huong Que. Bloomfield’s faves? 163 Vietnamese Sandwich and Galleria Umberto. Check out all the recs here.

👠🎃 The B-Side is a proud media sponsor of Night in the Stacks, the BPL’s iconic annual fundraiser. This year, the event is themed “Nightmare in the Stacks” given its timing on Halloween, and will include a band, dancing, food, and an open bar.

This incredibly fun event helps keep lights on and books open at our libraries — last year, the fundraiser brought in over $260k. Get going and check it out here!

Think YOU were a try hard in college? Meet 20-year-old Brookline native James Redding, who just became the youngest man ever to complete all six world major marathons … in under 18 months. 

It all started back in 2021 when Redding’s daily jog turned into 5k and 10k races … which turned into half marathons … which turned into him applying for Boston in 2024 … and the rest is history. A lot of fundraising, a few lucky lottery picks, and some clutch help from New Balance later, he somehow managed to run all six major marathons in about a year-and-a-half.

But even after traveling the world, Redding says Boston was his favorite. Check out the full story here.

— Written by Gia Orsino, Emily Schario, and Claire Nicholas

🏃 Thanks for reading! Maybe this is him just getting a head start on his quarter-life crisis.

💜 Special shoutout to today’s sponsor, the Museum of Fine Arts, Boston, for supporting local journalism and bringing culturally rich experiences to our city.

⚠️ The results are(n’t) in: There was no poll in yesterday’s newsletter. Our bad! To make it up to you, here’s a WILD $25 dinner deal we were going to keep exclusive to members.

💃 Keep up with us @BostonBSide on IG, TikTok, and Twitter. Send comments and suggestions to [email protected] or [email protected].